Two new sesquiterpenoids from the marine-sediment-derived fungus Trichoderma harzianum P1-4

References

• Ahluwalia V, Kumar J, Rana VS, Sati OP, Walia S. 2015. Comparative evaluation of two Trichoderma harzianum strains for major secondary metabolite production and antifungal activity. Nat Prod Res. 29(10):914–920.
   PubMed Web of Science ®Google Scholar
• Almassi F, Ghisalberti EL, Narbey MJ, Sivasithamparam K. 1991. New antibiotics from strains of Trichoderma harzianum. J Nat Prod. 54(2):396–402.
   Web of Science ®Google Scholar
• Cai F, Yu G, Wang P, Wei Z, Fu L, Shen Q, Chen W. 2013. Harzianolide, a novel plant growth regulator and systemic resistance elicitor from Trichoderma harzianum. Plant Physiol Biochem. 73:106–113.
   PubMed Web of Science ®Google Scholar
• Can DE, Iyengar R, Shiao MS. 1981. Cyclonerodiol biosynthesis and the enzymatic conversion of farnesyl to nerolidyl pyrophosphate. J Am Chem Soc. 103(4):914–931.
   Web of Science ®Google Scholar
• Corley DG, Miller-Wideman M, Durley RC. 1994. Isolation and structure of harzianum A: a new trichothecene from Trichoderma harzianum. J Nat Prod. 57(3):422–425.
   PubMed Web of Science ®Google Scholar
• Cutler HG, Cox RH, Crumley FG, Cole PD. 1986. 6-Pentyl-α-pyrone from Trichoderma harzianum: Its plant growth inhibitory and antimicrobial properties. Agric Biol Chem. 50(11):2943–2945.
   Web of Science ®Google Scholar
• Cutler HG, Jacyno JM, Phillips RS, VonTersch RL, Cole PD, Montemurro N. 1991. Cyclonerodiol from a novel source, Trichoderma koningii: plant growth regulatory activity. Agric Biol Chem. 55(1):243–244.
   Web of Science ®Google Scholar
• Evans R, Hanson JR, Nyfeler R. 1976. Studies in terpenoid biosynthesis. Part XVII. Biosynthesis of the sesquiterpenoids cyclonerodiol and cyclonerotriol. J Chem Soc, Perkin Trans 1 . 1(11):1214–1217.
   Google Scholar
• Ghisalberti EL, Hockless DCR, Rowland C, White AH. 1992. Harziandione, a new class of diterpene from Trichoderma harzianum. J Nat Prod. 55(11):1690–1694.
   Web of Science ®Google Scholar
• Claydon N, Hanson JR, Truneh A, Avent AG. 1991. Harzianolide, a butenolide metabolite from cultures of Trichoderma harzianum. Phytochemistry. 30(11):3802–3803.
   Web of Science ®Google Scholar
• Han MJ, Qin D, Ye TT, Yan X, Wang JQ, Duan XX, Dong JY. 2018. An endophytic fungus from Trichoderma harzianum SWUKD3.1610 that produces nigranoic acid and its analogues. Nat Prod Res.1–9. doi:10.1080/14786419.2018.1486311.
   Web of Science ®Google Scholar
• Langhanki J, Rudolph K, Erkel G, Opatz T. 2014 . Total synthesis and biological evaluation of the natural product (-)-cyclonerodiol, a new inhibitor of IL-4 signaling. Org Biomol Chem. 12(47):9707–9715.
   PubMed Web of Science ®Google Scholar
• Li X, Kim YH, Jung JH, Kang JS, Kim DK, Choi HD, Son BW. 2007. Microbial transformation of the bioactive sesquiterpene, cyclonerodiol, by the ascomycete Penicillium sp. and the actinomycete Streptomyces sp. Enz Microb Technol. 40(5):1188–1192.
   Web of Science ®Google Scholar
• Liang XR, Miao FP, Song YP, Liu XH, Ji NY. 2016. Citrinovirin with a new norditerpene skeleton from the marine algicolous fungus Trichoderma citrinoviride. Bioorg Med Chem Lett. 26(20):5029–5031.
   PubMed Web of Science ®Google Scholar
• Ma XY, Fang ST, Zhao Y, Ji NY. 2018. Chemical constituents of marine sediment-derived fungus Penicillium oxalicum T4-6 and their biological activities. Chem Bioeng. 35(1):17–22.
   Google Scholar
• Marfori EC, Kajiyama S, Fukusaki E, Kobayashi A. 2002. Trichosetin, a novel tetramic acid antibiotic produced in dual culture of Trichoderma harzianum and Catharanthus roseus Callus. Z Naturforsch. 57(5–6):465–470.
   Google Scholar
• Miao FP, Liang XR, Yin XL, Wang G, Ji NY. 2012. Absolute configurations of unique harziane diterpenes from Trichoderma species. Org Lett. 14(15):3815–3817.
   PubMed Web of Science ®Google Scholar
• Ordentlich A, Wiesman Z, Gottlieb HE, Cojocaru M, Chet I. 1992. Inhibitory furanone produced by the biocontrol agent Trichoderma harzianum. Phytochemistry. 31(2):485–486.
   Web of Science ®Google Scholar
• Reino JL, Guerrero RF, Hernández-Galán R, Collado IG. 2007. Secondary metabolites from species of the biocontrol agent Trichoderma. Phytochem Rev. 7(1):89–123.
   Google Scholar
• Shi ZZ, Miao FP, Fang ST, Liu XH, Yin XL, Ji NY. 2018a. Trichorenins A-C, algicidal tetracyclic metabolites from the marine-alga-epiphytic fungus Trichoderma virens Y13-3. J Nat Prod. 81(4):1121–1124.
   PubMed Web of Science ®Google Scholar
• Shi ZZ, Yin XL, Fang ST, Miao FP, Ji NY. 2018b. Two new isomeric tricycloalternarenes from the marine alga-epiphytic fungus Alternaria alternata K23-3. Magn Reson Chem. 56(3):210–215.
   PubMed Web of Science ®Google Scholar
• Song YP, Liu XH, Shi ZZ, Miao FP, Fang ST, Ji NY. 2018. Bisabolane, cyclonerane, and harziane derivatives from the marine-alga-endophytic fungus Trichoderma asperellum cf44-2. Phytochemistry. 152:45–52.
   PubMed Web of Science ®Google Scholar
• Suzue M, Kikuchi T, Tanaka R, Yamada T. 2016. Tandyukisins E and F, novel cytotoxic decalin derivatives isolated from a marine spong-derived fungus. Tetrahedron Lett. 57(46):5070–5073.
   Web of Science ®Google Scholar
• Vinale F, Gavin F, Sivasithamparam K, Lorito M, Marra R, Skelton BW, Ghisalberti EL. 2009. Harzianic acid, an antifungal and plant growth promoting metabolite from Trichoderma harzianum. J Nat Prod. 72(11):2032–2035.
   PubMed Web of Science ®Google Scholar
• Vinale F, Sivasithamparam K, Ghisalberti EL, Ruocco M, Woo S, Lorito M. 2012. Trichoderma secondary metabolites that affect plant metabolism. Nat Prod Commun. 7:1545–1550.
   PubMed Web of Science ®Google Scholar
• Zhang M, Liu J-M, Zhao J-L, Li N, Chen R-D, Xie K-B, Zhang W-J, Feng K-P, Yan Z, Wang N, Dai J-G. 2016. Two new diterpenoids from the endophytic fungus Trichoderma sp. Xy24 isolated from mangrove plant Xylocarpus granatum. Chin Chem Lett. 27(6):957–960.
   Web of Science ®Google Scholar
• Zhang M, Zhao JL, Liu JM, Chen RD, Xie KB, Chen DW, Feng KP, Zhang D, Dai JG. 2017. Neural anti-inflammatory sesquiterpenoids from the endophytic fungus Trichoderma sp. Xy24. J Asian Nat Prod Res. 19(7):651–658.
   PubMed Web of Science ®Google Scholar
• Zhu TH, Ma YN, Wang WL, Chen ZB, Qin SD, Du YQ, Wang DY, Zhu WM. 2015. New marine natural products from the marine-derived fungi other than Penicillium sp. and Aspergillium sp. Chin J Mar Drugs. 34:56–108.
   Google Scholar